Stereochemically controlled synthesis of 1,8-dioxaspiro[4.5]decanes and 1-oxa-8-thiaspiro[4.5]decanes by phenylsulfanyl migration

Article abstract of DOI:10.1016/0040-4039(96)00851-9

Single enantiomers and diastereoisomers of 2- and 3-alkyl-4- phenylsulfanyl-1,8-dioxa- and 1-oxa-8-thiaspiro[4.5]decanes can be prepared in good yield by acid-catalysed phenylsulfanyl migration. Either syn or anti stereochemistry can be selected by aldol reactions or by reduction of hydroxy-ketones.